


Forty Three One Night Stands, A Friend, A Boyfriend, And A Castiel

by DestielAddicted



Series: Non-Angst [2]
Category: Supernatural
Genre: ???? - Freeform, Alternate Universe - Romantic Comedy, Bisexual Dean, Bisexuality, Charlie Bradbury & Dean Winchester Friendship, Dean bottoms for older men, Dean is openly bi, Destiel - Freeform, F/M, Fluffy, Heterosexuality, Homosexuality, Light Angst, M/M, Male Homosexuality, Romantic Comedy, a break from my dark and depressing angst, brief Destiel, but dont worry, dean may or may not have a son, dont ask me if he has an std from sleeping around so much, enjoy it while you can, mentions of deanxamara, sassy cas at the end, vv brief, you know he does
Language: English
Status: Completed
Published: 2016-12-12
Updated: 2016-12-12
Packaged: 2018-09-08 01:12:56
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,385
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8824177
Author URL: https://archiveofourown.org/users/DestielAddicted/pseuds/DestielAddicted
Summary: Dean Winchester is a ladies man.Dean Winchester is also a man's man.But this isn't a story about his bisexuality. This is a story about how redemption can earn you some good karma, despite the little hiccups along the way.It's kinda about his bisexuality too though.





	

**Author's Note:**

> Here is a little romantic comedy type au for all of you who have been waiting for me to post since I ended Life Can Do Terrible Things. This has been a work in progress for months and I finally finished it. Now back to angst and depression and noncon I go!

Dean could admit when he was in the wrong. He could also admit that he'd been in the wrong for some time and that it was time for a change. He was watching TV when his roommate, and friend, unfortunately, Charlie proposed the idea to him, effectively blocking his view of another 'Dr. Sexy MD' rerun he hadn't seen before.

"Charlie, get out of the way, I gotta see if Dr. Sexy is gonna hook up with this redheaded nurse with the big cans or not," he said, trying to move in his seat on the couch to see around Charlie.

She grabbed the remote from Dean's hand, having to literally pry his fingers off of it in order to turn off the TV. He tossed it on the chair a few feet away and crossed her arms, a file in her left hand. Dean's curiosity was peaked.

"What's that?" he asked, nodding his head and raising his eyebrow.

"Your redemption, dear fool," she said with a smile that made Dean uneasy.

She smiled and walked over, sitting next to Dean and laying the file flat on her lap, opening it up to reveal a picture of a blonde in a black dress in a pose that Dean could only recognize as a mug shot. In a picture behind it, it looked like it was another, lower quality picture that deemed to be a shot from a hidden camera. He flipped through a few more pages, each one the same, but not every one had a mug shot, some were regular photos.

"What the Hell is this?"

"Since I'm a good person, and incredibly awesome - like, seriously, I'm so good at finding people that I should be in the FBI or CIA or something," Charlie said, grinning proudly.

"Is there a point to this?" Dean asked, raising his beer bottle to his lips.

"There is. This is a folder of all your ex one night stands, that can be accounted for at least."

Dean lowered the beer again and looked at Charlie, dumbfounded and, admittedly, a little impressed.

"You said you felt bad for all the people you 'humped and dumped' when you were going through that weird phase last year, so I took pity upon you, like the awesome friend that I am, you're welcome in advance by the way. I tracked most of them down, but a lot of them are basically ghosts now, either that or I'm losing my edge," she said, flipping through the pages.

There were a few pages of guys in the folder and Dean felt his ears burn in embarrassment as he leaned forward to set his beer bottle down on the coffee table. He snatched the folder to look through himself.

"There's some I couldn't find since your security cameras have shit quality, so they'll just have to live with it, but I found most of them through facial recognition software that I downloaded to my computer, don't tell anyone I did that because I'll probably get arrested. Lucky for you, most of them had criminal records," Charlie explained, pointing to the blonde with the mug shot who looked like she got arrested for fighting if the state of her hair was anything to go by.

"How many are there?" Dean asked dumbly, flicking through the pages.

The folder had to be at least an inch thick. That wasn't good.

"Around forty, so it looks like you've got a lot of houses to go to. Actually, there's a lot more than that but I also didn't account for the nights you've spent at other people's houses, so, really you've probably had over sixty, that also isn't accounted for one night stands outside of Lawrence. So, I guess what I'm saying is that this list is of one night stands, here in Lawrence, that spent the night here, and that I could find. Kinda specific, I know."

"Yeah - wait, what? What do you mean I've got a lot of houses to go to?" he asked, looking up from the folder at his friend, furrowing his eyebrows in confusion.

This was a lot to process.

"Yeah, you're going to each house on that list that I've found and you're going to apologize to that person for kicking them out in the morning and never calling them again."

Dean's cheeks flushed in embarrassment.

"How do you know I haven't called any of them?" he asked defensively.

"Because I knew asshole Dean, I still know him, and because I'm not stupid," she said, standing up.

"Clearly. I mean, you put together an entire friggin' folder - wait, where did you get their addresses?" he asked, standing up slowly and looking back down at the folder in bewilderment.

"It wasn't hard for the ones with mug shots or that were arrested, I got it from their police records and parole officer's computers. As for the others, I had to do some digging, and deduction, ugh, I've been watching too much Sherlock."

Charlie grabbed her jacket and slipped it on, crossing her arms.

"C'mon Romeo, let's go," she ordered, hovering over by the door.

Dean looked up from the folder and furrowed his eyebrows.

"We're starting now?"

"Yes...well, no. First you go change into presentable clothing, then we'll go," she said.

Dean looked own at his sweatpants and grey Metallica shirt for a second before nodding and sighing, handing her the folder as he walked off to change.

...

Once he had changed into a simple pair of jeans and a black shirt, he walked out with Charlie. He grabbed his worn brown leather jacket and pulled it on with a sigh, opening the door and dramatically motioning for her to walk out. They got into the Impala and drove off, Charlie telling him which turns to take to get to the first person's house. Once they had gotten there, he looked out the window and groaned in frustration, pulling the keys from the ignition.

"Do I have to do this?"

"Yes. Your ego has been spared for far too long my friend, it's time you swallow your pride and get your ass up there," she said, closing the folder with a smack of her hand.

Dean sighed, biting his lip in thought for a moment before looking at her with wide, pleading eyes.

"Come with me?" he asked, batting his eyelashes as if he were a child.

Charlie stared at him for a moment, and he could see her trying to fight it, but he ended up winning in the end when she groaned.

"You're such a pussy," she grumbled, unbuckling her seatbelt.

Dean smiled triumphantly and unbuckled his as well, getting out of the car and closing the door carefully. Charlie slammed the door and Dean whined.

"Hey! Don't slam my damn door!"

"I'll slam what I want, you're lucky I even did this for you."

Dean rolled his eyes and pouted as he followed Charlie up the steps and rang the doorbell. Charlie glanced over and smacked his arm softly, clutching the folder in her free arm.

"Stand straight," she demanded just as the door opened. "You're standing about as straight as Elton freaking John."

"Oh yeah, well you're as straight as-"

Someone cleared their throat and they both looked at the door, where a blonde woman stood with crossed arms.

"Hiya," Charlie started awkwardly, "um, you're Andrea, right?"

...

Seven houses later, and surprisingly only four angry exes, Dean flopped down into the driver's seat of Baby with a tired sigh.

"Charlie, I'm exhausted, can we go home?"

"C'mon big boy, you can't give up now! Hey, only two of them tried to spit on you!" Charlie said, far too cheery for Dean's taste.

Dean glared at her and brushed the phantom spit of that brunette off of his cheek. Charlie sighed, biting her lip and looking down at the papers.

"Okay, one more house so we're at an even number, and then we can go home for the night. But I expect extra hustle from you tomorrow," she said, pulling a paper from the file to look at.

It was already dark out -  Dean glanced at the clock and saw it was ten forty two - and Dean was ready to go home, but he could do one more house. He put the keys in the ignition and sighed, following Charlie's directions as she recited them. They pulled up in front of a light blue house and Dean stepped out of the car, closing the door. He smiled when Charlie didn't slam the door this time, figuring she was too tired to.

"Okay, her name is Amara Shurley and you guys-" Charlie started, but Dean interrupted her without thinking.

"Wait, I've heard that name before...Shurley I mean."

Charlie furrowed her eyebrows but shrugged, flipping through the pages.

"She's the only Shurley I have in here."

Dean tilted his head as he thought, but he couldn't come up with anything, but he knew he'd heard that name before, he could swear on it. Charlie rung the doorbell and hummed softly as they both waited. The door opened and a short man stood there, he was shorter than Charlie. His hair was curly and dark brown and he had a lame excuse for a beard on his face, and blue eyes that were as pale as ice, but somehow still warm with kindness.

"Dean Winchester?" the small man asked, a sense of underlying excitement in his voice, it was obvious he was trying to suppress some of it so his voice kept its calm ring.

Dean's eyes slowly widened and he felt heat rise to his cheeks. Shurley.

"It's me, Chuck."

Dean swallowed thickly and offered a small smile, scratching the back of his neck.

"Is Amara home?" Charlie asked bluntly, and Dean shot her a glare, but she shrugged.

"Uh, yeah, I...I think so," he turned and called for Amara towards the inside of the house before turning back to face the two. "Why-why do you need my sister?"

"She's your sister?" Dean asked almost immediately, a small sense of panic in his voice.

"Yeah," Chuck said and looked at Dean again. "Dean, how've you been?" he asked, his voice gentle, like he'd scare Dean off if he spoke any louder.

And he very possibly could have. Dean was spooked, so much so that he was ready to dart off like a rabbit on a road.

"Am...am I missing something here?" Charlie asked when Dean didn't respond.

"We...we dated for a while, in college," Chuck said, not even glancing at Charlie, keeping his eyes on Dean.

"Yeah, yeah we...we did. Uh, just...tell your sister I'm sorry, later Chuck," Dean rushed, turning on his heels and walking out.

He could hear Chuck calling him, and Charlie hot on his heels, but he didn't stop. They got into the car and Dean just sat in the passenger seat for a while, glancing through the passenger window to see Chuck watching him with sadness in his eyes. He drove out of there faster than he could let out the breath he'd been holding, speeding down the street and making a sharp turn. He was glad for Charlie's silence, he didn't feel like explaining and she didn't feel like pushing. They got home and Dean didn't even kick off his shoes before walking into his room and locking himself in for the night. He flopped down onto his bed and buried his face into the pillow. He'd unknowingly spent a night with the sister of the first guy he ever dated, and maybe loved, small world.

...

The next day when Charlie got up to wake up Dean, she found that his door was still locked. He knocked on it softly at first, but when it was clear that it was getting her nowhere, she started slamming her fist against it, not lighting up until she heard Dean groan from the inside. Dean dragged himself from the bed, hair a mess and clothes disheveled from sleeping. He opened the door and glared at her with bags under his eyes, rubbing the sleep from one eye as he looked at her.

"I can't do it again, Charlie," he said with a sigh, running a hand through his hair.

Charlie raised an eyebrow and crossed her arms.

"Like Hell you can't. You're Dean Winchester, if you can jump up on the table of a gay bar and demand someone be the Tonto to your Lone Ranger, you can handle a few one night stands," she said, her face still stern and determined.

"I was drunk off my ass and it was my birthday so give me a break and stop holding that against me," Dean argued, crossing his arms.

"I will forever hold that against you, and I'll also never let you forget that you let that southern guy-"

"Shut up."

"My point is, you're Dean Winchester, you can do anything you want," Charlie said encouragingly.

Dean pondered this for a moment, then spoke.

"Alright, I want to lay on the couch all day and watch Spanish soap operas."

"Don't be a smartass," the redhead said, shoving at Dean's chest lightly. "Now go get dressed."

Dean groaned and turned, slamming the bedroom door again. He pulled his shirt and jeans off, tossing them into the pile in the corner of his room with his boxers following. He found a new pair of boxers and quickly pulled them up his legs, the elastic hugging his hips. Just as he pulled another pair of jeans on, he heard Charlie's voice from behind the door again.

"Dean?"

"Yeah?"

"Who is Chuck...to you?"

Dean was silent for a moment, then pulled his shirt over his head and grabbed a belt, pulling the door open and walking past her silently. Charlie followed suit, curious, but not wanting to pry, mainly because Dean was bitchy when he was irritated.

"Could I have a brief summary? I mean, I told you about my summer love with Dorothy."

"Not the same," Dean snapped, then saw Charlie flinch slightly. "Not...not the same," he said, softer now once he saw her flinch from the harshness in his voice.

He grabbed his shoes and sat on the couch to pull them on. Charlie nodded slightly, leaning against the wall as Dean got ready. They left in silence.

...

"Dean, I didn't spend thirty seven hours doing this much research just for you to chicken out on-" she started, but was cut off sharply by Dean in a matter of seconds.

"Well I didn't ask you to do any research!" he snapped, glaring at her.

She sighed and leaned against the passenger door of the impala. Dean sighed and shook his head, rubbing his hands over his face.

"I'm...I'm sorry. I just...I don't wanna do this anymore. I mean, yeah, I feel bad still, but I can't run into any more..." he explained with a sigh, pacing around in circle.

"Any more Chucks?"

Dean sighed again, annoyed and frustrated.

"Are there any more Chucks to worry about?" she asked carefully, in case Dean was ready to snap again.

Dean didn't say anything, but he did shake his head. Charlie nodded and continued to watch Dean, who was looking at the floor as he chewed on his lip. They were silent for a long time, just standing in front of Lisa Braeden's house, Charlie carefully calculating what she was going to say next.

"He mattered to you, didn't he?" she finally asked, and Dean looked up at her slowly.

Dean nodded again, eyes dancing over the details in the cracks of the sidewalk under his feet. He hadn't thought about Chuck in at least eight or nine years, when they'd met in Dean's senior year of community college, Chuck was a good five years older than Dean, a teacher's aide at the time, a professor in training. Chuck had aged visibly, not that he still wasn't completely  fuckable in Dean's eyes, he definitely was.

"I get that you're not really the type to talk about your feelings and stuff, but it can be therapeutic sometimes, y'know?" Charlie said, sighing when Dean didn't say anything in response.

Dean looked over to Charlie where she reached into the car through the window and grabbed the manilla folder, she opened it up and flipped through a few pages before she pulled one out and walked back over. She handed the paper to Dean and he sighed when he looked at it. There was a picture of a brunette with a bright smile, Dean remembered her, oddly enough. Lisa Braeden.

"Charlie, I said-"

"We're already here. If it's too hard, we can stop."

Dean sighed. He glanced at the photo again before turning to look at the house behind them. He handed the picture back to Charlie and started up the walkway.

...

Much to his surprise, Lisa invited the two in for lunch. Of course neither of them could ever turn down a free meal, no matter how awkward the situation might turn out to be. Lisa set them up at the small dining table off of the kitchen and brought them some pizza.

"I wasn't expecting company, so I hope Domino's is okay," she said, chuckling a little.

"I love pizza, so I'm not complaining," Charlie said, shrugging as she took a bite.

Dean smiled slightly up at the brunette, taking a slice and setting it on the paper plate she had offered him. He had actually spent the night with Lisa a little more than a while back, but only by a few months. He definitely remembered that night, how could he forget the very bendy, adventurous yoga instructor?

"I didn't think I'd hear from you again," Lisa said as she sat down in a chair by Charlie, looking at Dean.

"Yeah well, my friend-" he started, but was interrupted when he felt Charlie kick him underneath the table.

He glanced at the redhead, who was currently glaring at him as she took another bite of pizza.

"My friend told me that I'm an asshole and that one night stands are 'disrespectful'," he lied, sighing and picking up the pizza.

"I don't believe that," Lisa said, surprising them both, "it isn't really disrespectful...unless you have like...some trophy list of one night stands."

Charlie looked at the manila folder that was sitting on the table beside her plate, then at Dean, eyes wide. Dean opened his mouth to speak, but was cut off by a high pitched whine that erupted from another room in the house. Lisa quickly excused herself and jogged off to the room the noise had come from. Dean looked at Charlie and they both shrugged, letting their curiosity get the best of them as they both stood up from the table and followed Lisa. They trailed her into a small room down the hall, directly across from what looked like the master bedroom.

The room was small, the walls painted a pastel blue, the curtains a plain white. There were dinosaur decals on the walls, toys scattered across the floor; reds and greens and rings and cars on the dark blue rug in the middle of the room. Lisa didn't seem to notice their presence as she bent over a dark brown crib and straightened again with a small boy in her arms. Dean's eyes widened, the boy was pale-skinned, light freckles scattered across his nose and cheeks. His eyes were deep brown like Lisa's, and he watched over his mother's shoulder, looking right at Dean.

"Uh..."

Lisa jumped slightly and turned when she heard Charlie, the small boy making a noise of protest when Dean was torn from his line of sight. He tried to turn to see him again, pushing at his mother's chest and turning his body, small legs kicking. Lisa set him down on the floor and he preoccupied himself with one of the toys at her feet.

"How...how old is he?" Charlie asked, because there was no way Dean could form words right now.

Dean saw the way Lisa hesitated, the way she licked her lips nervously and looked down at the boy.

"Almost thirteen months," she said after what seemed like way too long of a silence for Dean to handle.

Dean ran a hand over his mouth, eyes flickering down to the boy.

"His name is Ben," she said, crouching down and ruffling his hair, " and before you ask, he's not yours."

Dean didn't believe her, and by the looks of it, neither did Charlie.

"He looks like me," Dean said after a while, looking at Lisa with anger and hurt and sadness in his eyes, but all of the emotions were aimed at himself.

"I have a type, I...I guess," Lisa said, standing again.

The room was silent for a while before the boy looked up from his toy and looked right at Dean again, mouth hanging open and drool dripping down his chin as he stared. Dean watched the boy, staring right back at him and swallowing thickly. Dean had slept with Lisa a little over a year ago; it was very much possible that Ben could be Dean's kid. Dean felt a sense of pride, because he might have helped make this little human, he might have helped bring this kid into the world and he could have the chance to help raise him, he could do so much better than his father did. But, what if Lisa wasn't lying? What if this really wasn't Dean's child?

Was it just a coincidence that Lisa slept with another man with freckles and peach skin around the same time she had slept with Dean?

"Dean?" Charlie asked, bringing him out of the trance.

Dean broke the staring contest with the small child and turned to Charlie, opening and closing his mouth in an attempt to find the right words to say.

...

Dean didn't feel like going to anymore houses that day, and Charlie was okay with that. They didn't talk about the incident again for the rest of the night. They didn't talk about Lisa. They didn't talk about Ben. They didn't talk about the fact that Dean was probably a father.

They went to their separate rooms and each contemplated and digested the information.

Dean tried to tell himself that even if he was Ben's father, Lisa didn't seem to need, nor want, Dean around to help raise the young boy. Dean was okay with that, he really was. He wasn't good with kids anyways, he'd probably mess Ben up if he tried to raise him.

Dean sighed and rolled onto his side. Something in him didn't feel right.

...

It took a while before Charlie was able to convince Dean to get back out there and finish the list like they'd set out to do before all this inhibiting drama came in. In the nearly week and a half that Dean kept refusing to finish their quest, Charlie was thinking of ways that she could make it easier for Dean. She wished she could do more research on the different girls and boys burned by Dean alike, to try to seed out the ones that might be too emotional for Dean to handle. She was currently sitting on their couch, nearly engulfed in the worn out brown leather seating.

"Matilda...how do you even pronounce that last name? What, did you sleep with a witch or something?" Charlie asked as the two went through the different brief summaries in the manila folder.

"I met her at a costume party, I thought she was just really into the whole roleplay thing so I went with it, sue me."

"Beckham Kash? Is that a real name or is he into roleplaying as a douchebag?"

Dean took the paper and looked over it briefly.

"He was a frat guy I met when I crashed a college party with a few of my friends. He wanted to know what it was like to be with a dude, but he insisted that he wasn't gay, sure could suck dick though."

Charlie snorted.

"Louis McCellan," Charlie said once she picked up another piece of paper, "football star in training apparently?"

Dean looked over and shrugged.

"This is kinda fun, going through your sexual history, seeing the kinda people you hook up with," Charlie said, chuckling. "You don't seem to have a type..."

Dean shrugged again and tossed the paper back into the pile.

"Castiel Novak," Charlie announced, handing Dean a piece of paper, "he looks dreamy."

Dean took the paper and looked at it, smirking slightly.

"I actually remember him."

"You do?" Charlie asked with an overdramatic gasp.

Dean rolled his eyes and stared at the picture of the dark haired man, who was squinting at where the camera would have been in order to take the photo; it looked like a mugshot from how messed up the man's hair was and the fact that there seemed to be bags under his eyes. He let his eyes scan over the sheet of paper, but there wasn't any criminal history. It must have been a driver's license photo or something. He barked out a laugh and waved the paper at Charlie, pointing to a section near the bottom of the page.

"I remember him because see here? He took gymnastics for a few years, boy...he was bendy as Hell for a dude."

"Didn't need to know that, thanks," Charlie said, shoving the paper away.

Dean set the paper down and picked up another, moving on easily.

"Ah, here! Benjamin Lafitte, he lives right here by us, it's like a ten minute drive."

Dean looked at Charlie and sighed, taking the paper from her hands.

...

"God, this guy is like, ten years older than you Dean!" Charlie said as they both got out of the car and headed inside the apartment complex that had Benny's address in its halls somewhere.

Dean shrugged, blushing.

"Don't judge me."

They found apartment 27D and Dean knocked on the door, sighing tiredly as they waited for an answer. They heard shuffling from inside, and the door opened to reveal a tall, thicker man with a beard. He furrowed his eyebrows as he stared down at the redhead with the tan folder in her arms, then his eyes went to Dean and a grin broke out over his face.

"Dean," he said, voice curling in a southern drawl, "ain't seen you in a while."

Dean smiled slightly, cheeks light pink. He usually wasn't this nervous around guys, but then again, he usually didn't bottom or beg for a guy's dick as much as he had for Benny.

"Benny," Dean said, nodding his head once.

They were silent, all three of them just looking at each other. Charlie shifted the folder in her arms so it was under one of her armpits and she held out her hand for the burly man.

"Nice to meet you Sir, I'm Charlie Bradbury."

"What are you doing?" Dean asked, smacking her hand lightly.

"I don't know, he reminds me of my dad so I thought I'd be respectful."

They both heard Benny chuckle as he shook Charlie's smaller hand.

"Benjamin Lafitte. Dean, show this young lady some respect," he said, "someone as beautiful as her deserves it."

Charlie grinned smugly at Dean and stuck her tongue out at the blonde.

"Don't bother, Benny, she's lesbian," Dean said, and Benny raised an eyebrow.

"Doesn't mean she don't deserve respect, you of all people should know that."

Dean blushed and crossed his arms.

"Y'all wanna come in for a bit?" Benny asked, finally letting go of Charlie's hand.

Both Charlie and Dean had very different answers, but they ended up going in anyways.

...

They left Benny's apartment a while later, because Benny had to get to work. Dean was relieved once he was finally in the safety of his car again, he sighed and closed his eyes.

"We aren't done, are we?" he asked, leaning back in the driver's seat.

"We've got eight more houses left for today, then we can go back home."

Dean sighed, muttered a curse, and started the car up.

...

Bela Talbot's house was large, it had at least three stories and the premises was guarded by large, black gates that had the letter 'T' on the front of them. Dean pulled up in front of them and cursed, looking at the little box where he was supposed to punch in numbers that would open the gates so they could enter. The house itself was very modern looking, made up of blocks of red and brown stacked on top of each other. One room wasn't even painted, it was just glass all around. The front yard was covered in vibrant green grass, hedges trimmed into shapes lining the walkway to the front doors. The front doors were black, and he couldn't exactly tell from here, but they looked about twice his height.

These people must shit gold blocks.

He didn't remember Bela or their night together all to well, but he certainly didn't know that she was loaded. He had assumed that she had some money, since when they first met in that shitty hipster dance club she had been dressed like she drove around in a topless car in Beverley Fucking Hills or something. Dean remembered her outfit all too well for someone he'd barely wined and dined months ago. She had been wearing a bright white, and very tight cocktail dress, and Dean had literally blessed the Lord when she crossed her legs at the bar stool she was sitting on and the already very short dress rode up on her thighs the slightest bit. She'd been wearing a long, navy blue trench coat earlier in the night, but when Dean approached her, it was tossed over the back of her chair.

Bela had long, light brown hair. When Dean met her, it was curled in loose ringlets and pulled over her shoulder. Her lips were maroon and her teeth were blinding white when she smiled at the approaching Dean. Her whole face was done up in make up, but Dean had the feeling that even if she hadn't been wearing all of it, he'd still bang her. Her eyelashes were ridiculously long and smoky grey and maroon highlighted her dark green eyes.

Basically, Bela was hot. But, she was also a bitch.

She was bossy in bed, and that's not what Dean minded, because it was nice to have a partner take control once in a while, just look at him and Benny, but she was just plain rude. To make matters worse, Dean woke up the next day to his cellphone and money from his wallet missing.

Dean pressed angrily at the button on the little box of numbers, and it kept buzzing.

"Who the Hell are you and what is so urgent that you have to bother me?" came a voice from the speaker next to the buttons.

It was Bela's voice.

"I'm here for my money, you bitch-" Dean lied, and Charlie hit his arm.

There was a pause, then the box buzzed and the gates opened.

...

Dean pounded angrily on the front doors, which he ended up being right about, they were twice his height and only slightly intimidating.

Okay, very intimidating.

One of the heavy doors opened and Bela crossed her arms as she looked at Dean.

"What money?" she asked, face emotionless.

"The money you took from me."

Bela looked over at the redhead beside Dean and winked, making Charlie's cheeks go pink.

"Honestly, if it's taken you this long to notice then you're even slower than I thought."

Dean squinted angrily.

"You're cute when you're angry, we should shag again after this..." Bela said, smirking.

Dean huffed, crossing his arms to match hers.

"Don't objectify me." he said, earning a snort from Charlie.

The two hotheads glared at each other for a while before Charlie cleared her throat and they both turned their heads to look at her. She looked at Dean expectantly.

"Hell no, next house," Dean said, turning and stomping back over to the Impala.

Charlie glanced back at Bela nervously before scurrying to follow Dean. The brunette rolled her eyes before closing the door again and receding back into her house.

...

They tackled a few more houses over the span of a few days, and after what seemed like forever, they were finally down to the last three or four.

"Finally, this Hell is almost over," Dean muttered and knocked loudly on the solid white door of a condo on the outskirts of town.

Charlie chuckled and held the folder in her arms. They were silent for a while, Dean staring at the small welcome mat beneath their feet. It was brown with a picture of a small bee flying around a hive, and it said 'Welcome to my hive!' in large letters, Dean snickered at it. What kind of loser has a mat like that?

"Thanks, by the way..." Dean muttered after a while.

Charlie glanced at Dean, smiling softly, she didn't even have to ask what he meant by it, she knew.

"You're very welcome."

They stood in silence again and Dean sighed in annoyance, knocking on the door once more, with more urgency.

"Who's place is this again?" he asked, grabbing the folder and looking at the paper sticking out.

He saw that it was Castiel Novak, aka, the king of bendy positions. He couldn't help but stare at the picture and grin, the dude just looked so serious that it was funny to Dean. He put the paper back in the folder and kicked the mat slightly.

"Look at this mat, it's so stupid."

Just then, the door swung open and Dean turned his head to see a very confused looking man with bright blue eyes and dripping wet hair standing there, a towel wrapped around his waist.

God bless those hipbones, Dean could just remember how much time he spent with his hands or mouth on them just by looking at them.

"I'm sorry for the inconvenience, I didn't hear you knocking at first, I was in the shower." Castiel said, and Dean shrugged, tearing his eyes away from that damn towel to meet the man's eyes.

"No problem, wish I coulda joined you..." Dean said with a smirk.

Charlie kicked his calf and he glared at her.

"How may I help you?" Castiel asked, looking between the two curiously.

Dean looked a little shocked, because maybe, just maybe, he had hoped Castiel remembered him from their heated night together. But Castiel didn't, and Dean supposed that was the world flipping him off for all the times he'd forgotten hookups. It bummed him out, because he remembered every second on that night with this sexy bastard. Maybe he could just remind him...

"He's Dean Winchester, you guys hooked up a while back..." Charlie butted in, and Dean turned to give her a look. "Well, you weren't saying anything."

Castiel looked at Dean and studied him for a moment, his strikingly oceanic blue eyes inspecting Dean, poking and prodding wordlessly as he racked his brain for the memory. After a wile, Castiel's face lit up in what must have been realization and he smiled.

"I remember, you preformed anilingus on me," Castiel said.

Dean squinted slightly in confusion. "What?"

"You put your mouth on my anus," Castiel explained, and Charlie gagged slightly, making Castiel turn to look at her. "What? It is very pleasurable, you should try it, Dean is very good at it."

Dean's face was almost as red as Charlie's hair.

"Lesbian and no!" Charlie shouted.

There was a pounding down the hallway and someone yelled.

"Come inside, my neighbors don't like noise."

...

Castiel had dried off and gotten dressed before bringing the two a cup of coffee each, then sat down on his small, light blue chair across from them.

"A redemption plan, that's very noble," Castiel said, flipping through the folder.

"Yeah," Dean said, sipping the coffee and trying to ignore the fact that his cheeks were still pink from what Castiel had revealed to Charlie. "It was her idea, really..."

Charlie shook like she had been traumatized, sipping her coffee silently.

"Well, you don't have to say it with me, I already forgive you. I understand some people aren't one to have relationships or aren't able to form bonds with others well, so they turn to mindless, meaningless, and anonymous sex."

Dean nodded slightly, mentally trying to figure out if he was supposed to be offended by that or not.

"Although, you shouldn't suppress feelings your whole life, it only leads you down paths of destruction and self loathing," Castiel added, looking right at Dean.

"Y-yeah..."

They were silent for a while, Castiel's eyes boring into Dean's until the blonde man looked away at something suddenly very interesting on the wall.

"I hope this isn't too forward Dean, but I'd like to take you out on a date."

Dean looked back at Castiel, eyes wide and eyebrows furrowed. he felt someone kick him underneath the table and looked over at Charlie, who was sipping from her coffee and not so innocently smiling behind the mug. Dean looked at Castiel again and swallowed thickly.

"Don't you hate me? I mean...you left me your number and I just...I threw it away..."

Castiel shrugged. "Then give me your number."

Dean sighed slightly, contemplating before he nodded and grabbed a pen from a white cup on the table. Castiel handed him a notepad and watched Dean scribble numbers onto it before handing it over to Castiel.

Castiel smiled.

"I hate to throw you both out now, but I have to get to work. I'll text you, Dean."

The three all got up and walked to the door, Charlie walking out first. Dean and Castiel exchanged small smiles before Dean turned to walk out, scratching the back of his neck.

"Oh, and Dean," Castiel started, making Dean turn to look at him, "my welcome mat is not stupid."

Castiel closed the door with a mocking smile.

Charlie laughed at Dean the whole ride home.

**Author's Note:**

> [my tumblr](http://sinthusiast.tumblr.com/)


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